Prior to the present invention, certain benzoylureas and their use as insecticides have been described in the literature. For example, U.S. Pat. Nos. 3,748,356; 3,933,908 and 3,989,842 which issued to Wellinga et al. described a series of substituted benzoylureas as having strong insecticidal activity. Wellinga et al claim compounds which are generally 1-(2,6-dihalobenzoyl) -3-(substituted phenyl) ureas with the phenyl ring being optionally substituted by halogen, lower alkyl, lower polyhaloalkyl or nitro.
A number of prior art, references discuss the insecticidal activity of the Wellinga et al compounds. For example see Van Daalen et al, J. Agr. Food Chem., 21, 346 (1973), ibid, 21, 993 (1973), and Malden et al Pestic Sci, 4, 737 (1973).
Studies in the inhibiton of insect development by the action of 1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl) urea and 1-(3,4-dichlorophenyl)-3-(2,6-dichlorobenzoyl) urea have been reported by Van Eck, Insect Biochem., 9, 295 (1979), Kev, Pestic Sci, 9, 259 (1978) and Grosscurt, ibid, 9, 373 (1978).
Further, in the prior art U.S. Pat. Nos. 3,992,553 and 4,041,177 describe 1-(phenoxyphenyl)-3-benzoylureas as insecticides.
Several literature references describe the preparation and insecticidal use of 1-heterocyclyl-3-benzoylureas. For example see A. B. DeMilo, et al, J. Agric. Food Chem., 26, 164 (1979) and K. Kramer, et al, Environ. Ent., 8, 274 (1979). In general, these investigations have found that while this class of compounds do exhibit insecticidal properties, they are not as active as the 1-phenyl-3-benzoylureas found in the above references.
The patent literature has also disclosed the compositions and insectidal utility of 1-(substituted pyridyl)-3-benzoyl-ureas in U.S. Pat. No. 4,173,639 and G.B. Pat. No. 2,028,813 (to Eli Lilly), U.S. Pat. No. 4,212,870 (to Gulf Oil) and in J. Kokai 78 11,537 (to Ishihara Sangyo). 1-Pyrazinyl-3-benzoylureas have been disclosed by Eli Lilly in U.S. Pat. Nos. 4,083,977 and 4,160,834. Gulf Oil has patented 1-thiazoyl-3-benzoylureas in U.S. Pat. No. 4,164,581.
U.S. Pat. Nos. 4,148,977 and 4,160,902 discloses substituted N-(phenylaminocarbonyl) pyridine carboxylates as well as their use to control insects.
Finally, applicant's copending application Ser. No. 305,951 filed Sept. 28, 1981 discloses certain 1-(bicyclooxyphenyl)-3-benzoylureas and their use as insecticides. Prior to the present invention, however, there was no disclosure of 1-(bicyclooxyheterocyclyl)-3-aroylureas of the class hereinafter indicated.
Accordingly, one or more of the following objects will be achieved by the practice of this invention. It is an object of this invention to provide novel bicyclooxyheterocyclyl aroyl ureas. Another object of this invention is to provide certain 1-(bicyclooxyheterocyclyl)-3-aroyl ureas which exhibit insecticidal activity. A still further object is to provide novel urea compounds, such as 1-(2-[4-chloro-1-naphthoxy]-5-pyridyl)-3-(2,6-difluorobenzoyl) urea and 1-(3-bromo-2-[4-dimethylamino-5,6,7,8-tetrahydro-1-naphthoxy]-5-pyridyl)-3 -2(chlorobenzoyl) urea. Another object is to provide processes for the preparation of the novel ureas. A further object is to provide novel pesticidal compositions containing the novel ureas as the active toxicant. Another object of the invention is to provide a method for controlling pests by the application of the novel pesticidal compositions. These and other objects will readily become apparent to those skilled in the art in the light of the teachings herein set forth.